Acetic Acid → HCID 59201718, compound

HRID 451754Notes

Reaction equation

HRID 451754 reaction equation
[CH:1]1([C@H:7]([OH:22])[C@H:8]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:9]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[CH3:27][NH2:28]>C1COCC1>[CH:1]1([C@H:7]([OH:22])[C@H:8]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH2:9][NH:28][CH3:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6329MethylamineHCID 59201687HCID 59201687, compound

Product 1

HCID 59201718HCID 59201718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Crude (2S,3S)-3-cyclohexyl-2-(1,3-dioxoisoindolin-2-yl)-3-hydroxypropanal (3.22 g, 10.7 mmol, calculated according to theoretical yield) was dissolved in anhydrous THF (20 mL). The solution was cooled to 0° C. Acetic acid (5.5 mL, 90 mmol), methylamine solution (33% in EtOH, 5.0 mL, 40.0 mmol) and NaHB(OAc)3 (8.80 g, 40.0 mmol) were added sequentially and in single portions. The ice bath was removed and the mixture was stirred for 2 h at rt. The solvent was stripped and the crude 2-((1S,2R)-1-cyclohexyl-1-hydroxy-3-(methylamino)propan-2-yl)isoindoline-1,3-dione (6.45 g) was used directly in the next step.

Workup

  1. customThe ice bath was removed

Sources & evidence

ORD record
ord-ef344ac9e56340b5ac101edd2c3b4c91
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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